Business Exit Strategy Planner
Build a comprehensive exit strategy for your business — whether you're planning an acquisition, merger, management buyout, or orderly wind-down — with valuation frameworks, timeline, and preparation checklists.
Prompt Template
You are a business exit advisor who has guided 50+ founders through successful exits. Help me plan an exit strategy for: **Business type:** [e.g., SaaS, e-commerce, agency, manufacturing] **Annual revenue:** 0 **Annual profit/EBITDA:** 0 **Years in operation:** [number] **Team size:** [number] **Growth rate:** [% year-over-year] **Why exiting:** [e.g., retirement, burnout, new venture, market timing, partner dispute] **Preferred exit type:** [acquisition / merger / management buyout / IPO / liquidation / unsure] **Ideal timeline:** [e.g., 6 months, 1-2 years, 3+ years] **Current state of the business:** [owner-dependent vs. runs without you, documented processes vs. tribal knowledge] Provide: 1. **Exit readiness assessment** — score across 8 dimensions (financials, team, documentation, customer concentration, legal, scalability, owner dependency, market timing) with specific gaps to close 2. **Valuation estimate** — using relevant methods for the business type (revenue multiple, EBITDA multiple, DCF) with comparable benchmarks 3. **Exit type recommendation** — which exit path maximizes value given the current situation, with pros and cons of alternatives 4. **12-month preparation roadmap** — quarter-by-quarter actions to increase business value and attractiveness before going to market 5. **Owner dependency reduction plan** — specific steps to make the business run without you (the #1 value killer in small business exits) 6. **Due diligence preparation checklist** — every document and data room item a buyer will request 7. **Deal structure basics** — cash vs. earnout vs. equity roll, and what to watch for in each 8. **Advisory team** — which professionals you need (M&A advisor, attorney, CPA, wealth manager) and when to engage them 9. **Post-exit considerations** — non-compete terms, transition period, tax planning, and what to do with the proceeds
Example Output
Exit Strategy — CloudSync (B2B SaaS)
**Revenue:** .4M ARR | **EBITDA:** K | **Growth:** 35% YoY | **Team:** 14
Exit Readiness Score: 6.2/10
| Dimension | Score | Notes |
|-----------|-------|-------|
| Financials | 8/10 | Clean books, strong margins |
| Team | 7/10 | Good, but CTO is a single point of failure |
| Documentation | 5/10 | SOPs exist for support, not for engineering or sales |
| Customer concentration | 4/10 | Top 3 clients = 42% of revenue 🚨 |
| Legal | 6/10 | IP assigned properly, but employee agreements need updating |
| Scalability | 7/10 | Architecture scales, but onboarding is manual |
| Owner dependency | 4/10 | Founder handles all enterprise sales 🚨 |
| Market timing | 8/10 | B2B SaaS multiples strong in current market |
Valuation Estimate
| Method | Multiple | Estimated Value |
|--------|----------|-----------------|
| Revenue multiple (5-8x for SaaS at 35% growth) | 6.5x | .6M |
| EBITDA multiple (12-18x for SaaS) | 15x | .2M |
| **Blended estimate** | | **-16M** |
12-Month Preparation Roadmap
**Q1:** Hire VP of Sales to take over enterprise relationships. Begin SOPs for all departments.
**Q2:** Diversify revenue — no single client above 15%. Clean up legal (employment agreements, IP).
**Q3:** Engage M&A advisor. Prepare data room. Begin buyer outreach.
**Q4:** Negotiate LOIs. Due diligence. Close.
Owner Dependency Reduction
1. Hire VP Sales and co-sell for 90 days before full handoff
2. Document your decision-making frameworks (pricing, partnerships, roadmap)
3. Appoint an operational leader who runs weekly team meetings
4. Remove yourself from day-to-day Slack channels for 30 days as a stress test
Due Diligence Checklist
- [ ] 3 years of audited financials
- [ ] Customer list with contract terms, renewal dates, and LTV
- [ ] Employee roster with compensation, equity, and key-person risk
- [ ] IP ownership documentation
- [ ] All vendor and partner contracts
- [ ] Churn data with cohort analysis
- [ ] Technical architecture documentation
- [ ] Legal: incorporation docs, cap table, any litigation
Tips for Best Results
- 💡Start preparing 12-24 months before you want to exit — rushed exits leave significant money on the table
- 💡Customer concentration above 20% for any single client is a red flag for buyers — start diversifying immediately
- 💡The #1 thing that kills deal value is owner dependency — if the business can't run without you for 30 days, it's not ready to sell
- 💡Ask for a "tax-optimized exit" analysis separately — the difference between asset sale and stock sale can be hundreds of thousands of dollars
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